Heptane → HCID 17806677, compound

To a solution of methyl 1-benzyl-1H-pyrrole-2-carboxylate (3.00 g, 13.9 mmol) in DCM (70 mL) at −78° C. was added a 1M solution of diisobutylaluminum hydride (DIBAL-H) in heptane (35.0 mL, 34.8 mmol). After 45 min the reaction was quenched with saturated aqueous solution of NH4Cl (20 mL) and Rochell's salt (100 g). The mixture was allowed to warm to rt and was stirred for 2.5 h. The reaction mixture was extracted with EtOAc (3×). The combined organic layers were washed with H2O, saturated aq NaCl, dried over MgSO4, filtered and concentrated in vacuo to give a pale yellow oil. The crude product was chromatographed over silica gel (0 to 20% EtOAc in heptane over 20 min) to give (1-benzyl-1H-pyrrol-2-yl)-methanol as a colorless oil (2.30 g, 88%). Rf=0.47 (1:1 heptane/EtOAc); 1H NMR (400 MHz, CDCl3) δ (ppm) 7.27-7.35 (m, 4H) 7.08-7.10 (m, 1H) 7.06-7.08 (m, 1H) 6.73 (dd, J=2.7, 1.8 Hz, 1H) 6.19 (dd, J=3.5, 1.8 Hz, 1H) 6.12-6.16 (m, 1H) 5.21-5.23 (s, 2H) 4.53 (d, J=5.1 Hz, 2H).

1. customAfter 45 min the reaction was quenched with saturated aqueous solution of NH4Cl (20 mL) and Rochell's salt (100 g)
2. extractionThe reaction mixture was extracted with EtOAc (3×)
3. washThe combined organic layers were washed with H2O, saturated aq NaCl
4. dry with materialdried over MgSO4
5. filtrationfiltered
6. concentrationconcentrated in vacuo
7. customto give a pale yellow oil
8. customThe crude product was chromatographed over silica gel (0 to 20% EtOAc in heptane over 20 min)

ORD record

ord-04fe4e43fbee4af8802f30dc52b00577

Source dataset

uspto-grants-2011_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07884124B2